Potassium Carbonate → HCID 87322724, compound

HRID 2239703Notes

Reaction equation

HRID 2239703 reaction equation
CC1C=CC(S([O:11][CH2:12][CH2:13][NH:14][C:15]2[C:16](=[O:32])[N:17]([C:28]([CH3:31])([CH3:30])[CH3:29])[S:18](=[O:27])(=[O:26])[C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=O)=O)=CC=1.[CH3:33][S:34]([O:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)(=[O:36])=[O:35].C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:33][S:34]([O:37][C:38]1[CH:39]=[CH:40][C:41]([O:11][CH2:12][CH2:13][NH:14][C:15]2[C:16](=[O:32])[N:17]([C:28]([CH3:29])([CH3:30])[CH3:31])[S:18](=[O:27])(=[O:26])[C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:42][CH:43]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5729984-Hydroxyphenyl methanesulfonateHCID 866258662-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4-methylbenzenesulfonate

Product 1

HCID 87322724HCID 87322724, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

2-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4-methylbenzenesulfonate (150 mg, 0.313 mmol) was dissolved in dry MeCN (3 mL) under nitrogen atmosphere. 4-Hydroxyphenyl methanesulfonate (65 mg, 0.345 mmol) was added followed by potassium carbonate (217 mg, 1.567 mmol). The reaction mixture was heated in a microwave reactor at 120° C. for 15 mins. Potassium carbonate was filtered off and the reaction mixture was evaporated to dryness in a vacuum centrifuge. The crude product was purified by preparative HPLC affording the title compound (61 mg, 38.5%). 1H NMR (CDCl3, 500 MHz): δ 1.73 (s, 9H), 3.11 (s, 3H), 3.23-3.27 (m, 2H), 3.83-3.86 (m, 2H), 5.65 (bs, 1H), 6.83 (d, 2H), 7.20 (d, 2H), 7.43-7.46 (m, 3H), 7.50-7.54 (m, 2H); 13C NMR (CDCl3, 125 MHz): δ 27.83, 37.34, 43.30, 61.85, 66.50, 108.27, 115.77, 123.48, 125.07, 129.07, 130.06, 131.68, 135.18, 143.35, 157.21, 159.65; Mass Spectrum: M+NH4+511.8.

Workup

  1. filtrationPotassium carbonate was filtered off
  2. customthe reaction mixture was evaporated to dryness in a vacuum centrifuge
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-f16b6c51a8804f4abcc173795bda78e3
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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